In this episode, Kate sits down with a woman she calls Ally, a former "trophy wife" who gave up everything when she realized she wasn't living her authentic life. Ally didn't want to be identified by name or expose others who were involved in this story because. . . people got hurt. This is an episode about how Ally struggled to reconcile feminism and wife/motherhood, personal freedom and security, as well as the "grass is always greener" myths surrounding romantic relationships and singledom.

Kate also discusses her own struggle with losing the independence and freedom that comes with detachment before marriage and children, as well as the pressures faced by unmarried women in their 20s and 30s and beyond. It's an episode that deals with the personal struggles we have inside and outside our relationships, and how to evolve in an authentic way when we are bound to interpersonal commitments.

This is an episode for anyone who is in a committed relationship who reminisces about what life used to be like before marriage, or children, or falling in love… who sometimes pines for freedom and independence, the joy of being completely untethered. And, it is for anyone who is single who thinks that maybe their life isn’t quite complete yet because they are still looking for their life partner, a better half.

It’s about the myths and stories we tell ourselves about the other side. It’s about the before and after, the looking back, and the looking ahead. It’s also about freedom and security and the many ways we have to choose one over the other.